Method for preventing electrification of synthetic high polyamides

ABSTRACT

Synthetic high polymers, such as polyamides, polyolefins, polystyrenes, polyvinyl chloride, polyvinylidene chloride, copolymers thereof and polymer blends thereof can be prevented from electrification by incorporating homogeneously imidazole or its derivatives into said high polymers. The amount of the imidazole or a derivative thereof added is 0.005 to 20 percent by weight based on the amount of the high polymer.

United States Patent Satoshi Ando Osaka;

Kyoichi Fujimura, Ibaraki, both of Japan 724,266

Apr. 25, 1968 Dec. 7, 1971 Kanegaluchi Boseki Kabushiki Kaisha Tokyo,Japan;

Snia Viscosa Societa Nazionale lndustria Applicazioni Viscosa Milan,Italy May 5, 1967 Japan July 8, 1967, Japan, No. 42/413891 InventorsAppl. N 0. Filed Patented Assignees Priorities METHOD FOR PREVENTINGELECTRIFICATION 0F SYNTHETIC HIGH POLYAMIDES 2 Claims, No Drawings US.Cl 260/78 R, 57/140 R, 260/78 A, 260/78 L, 260/78 S, 260/9l.7

R, 260/92.8 A, 260/93.5 A, 260/93.7 R, 260/94.9

GD, 260/DIG. l5, 260/DIG. 19

OTHER REFERENCES Korshak et al.- Synthetic Hetero-Chain Polyamides,1964, pp. vii, 9, 12, 158, 199,440

Primary Examiner-Harold D. Anderson AnomeyStevens, Davis, Miller &Mosher ABSTRACT: Synthetic high polymers, such as polyamides,polyolefins, polystyrenes, polyvinyl chloride, polyvinylidene chloride,copolymers thereof and polymer blends thereof can be prevented fromelectrification by incorporating homogeneously imidazole or itsderivatives into said'high polymers. The amount of the imidazole or aderivative thereof added is 0.005 to 20 percent by weight based on theamount of the high polymer.

METHOD FOR PREVENTING IILECTRIFICATION OF SYNTHETIC HIGH POLYAMIDES Thepresent invention relates to a method for preventing electrification ofa synthetic high polymer selected from the group consisting ofpolyamides, polyolefins, polystyrenes, polyvinyl chlorides,polyvinylidene chlorides and copolymers thereof, and polymer blendsthereof. I

Polyamides are hydrophobic as polyesters, polyolefins and the othersynthetic polymers, so that they have a high volume specific resistanceand cause a remarkable electrification phenomenon by a slight frictionand provide various electrostatic hazards.

Particularly, in production of fibers the electrification phenomenoninfluences highly on the quality of the fibers and the operationefficiency. For example, in any step of spinning, drawing, twisting,unwinding, warping, knitting, and weaving and also in products, thefilaments are stuck to or coiled round materials to be rubbed with thefilaments, or the filaments are repelled mutually, so that theunevenness of draft, yam breakage, fluffy, etc. are formed and thereforenormal operation in each step is retarded and further various drawbacks,for example, decrease of quality in products, deterioration of productdue to deposited dusts and unpleasant feeling to human body are caused.In order to improve these drawbacks, a large number of proposals havebeen made.

Namely, methods of applying compounds having antistatic ability to thehigh polymer, specifically to the polyamides, for example, processeswherein an addition product of an organic sulfamide with an alkyleneoxide, an addition product of an organic carboxylic acid alkanolamidewith an alkylene oxide, phosphoric acid partial ester of an additionproduct of an aliphatic alcohol with ethylene oxides or the sodium saltsthereof, a composition consisting of water soluble polyglycidyl etherand water soluble amine, a quartemary ammonium compound phosphoric acidester amine salt (U.S. Pat. No. 2,676,l22), a composition consisting ofpolyamine and polyepoxide US. Pat. No. 2,982,751), N-substituted a-aminodicarboxylic acid disaster, an ester of polyethyleneglycol and itaconicacid, or an alkylester of lysine, aspartic acid or glutamic acid isapplied on polyamide, in an aqueous solution or emulsion form or thenthe thus applied polyamide is further subjected to a dry heat treatmentto prevent the generation of static electricity.

Furthermore, recently a method for incorporating a compound havingantistatic ability in polyamide, namely a method wherein 0.5-1.0 percentby weight of a metal salt of phosphoric acid ester of an aliphaticalcohol or an addition derivative of an aliphatic alcohol with ethyleneoxides is mixed with the molten polyamide and the resulting mixture isspun to make the polyamide antistatic, has been proposed.

However, according to such methods for preventing electrification, theantistatic agent is removed by washing with water or cleaning ofpolyamide shaped articles, so that the antistatic effect is graduallydecreased or completely eliminated and therefore, the antistatic effectof these methods are temporarily and further, these methods accompanydrawbacks of discoloration of polyamide and worsen the touch.

Furthermore, when these antistatic agents are incorporated in polyamidein melt-extrusion, defects of yarn breakage in melt-spinning, formationof knobs and decrease of strength and elongation due to uniformdispersion of these antistatic agents and further drawbacks of increaseof friction resistance and stain due to leaching of the antistaticagents occur, so that these methods for preventing electrification needa further improvement.

In addition, when other high polymers are concerned with, for example,in a process of treatment with alkyl imidazoline derivatives, the effectis decreased as the shaped articles are rubbed and further such agent isreadily removed by washing with water and cleaning and the like.

On the contrary, the process, wherein antistatic agent is mixed anddispersed in synthetic high polymers, durability against washing withwater, cleaning and the like is higher than the after-treatment processas described above, but this process is not always satisfactory in viewof dispersibility, heat stability and discoloration.

The inventors have made many investigations for the purpose of solvingthe above-described problems and the present invention has beenaccomplished.

Namely, the object of the present invention is to provide polyamides,polyolefins, polystyrenes, polyvinyl chlorides, polyvinylidene chloridesor copolymers thereof, or polymer blends thereof having an excellentantistatic property.

The other object of the present invention is to provide a method forproducing easily the above-described synthetic high polymers orcopolymers thereof or polymer blends thereof having an excellentantistatic property.

The above-described objects can be attained by incorporatinghomogeneously imidazole or its derivatives having the general formulawherein R,, R R and R represent hydrogen, alkyl group, aryl group,aralkyl group, cycloalkyl group, carboxyl group or its metal salt,esterified carboxyl group, alkylcarbonyl group, oxyalkyl group, aminogroup, acetamide group, alkylamino group, arylamino group or itsacetyllate or sulfo group and besides R may be mercapto group, halogenor halogenated alkyl group and R and R may be nitro group, aldehydegroup, halogen or halogenated alkyl group, into a synthetic high polymerselected from the group consisting of polyamides, polyolefins,polystyrenes, polyvinyl chlorides, polyvinylidene chlorides, andcopolymers thereof and polymer blends thereof.

The imidazole or its derivatives to be used in the present invention arethose which are durable to the temperature and the pressure inproduction and melting of the synthetic high polymer irrelative to thesubstituents, for example, l-pentyl imidazole, l-ocytyl imidazole,l-phenyl imidazole, l-benzyl imidazole, l-butyl-2,4,5-trimethylimidazole, S-amyl-l-methyl imidazole, 4,5-dipropyl imidazole,l-ethyl-Z-hendecyl imidazole, l-methyl-2-tetradecyl imidazole,l-methyl-Z-pentadecyl imidazole, 2-phenyl imidazole, 2-decyl imidazole,2- undecyl imidazole, 2-tridecyl imidazole, Z-tetradecyl imidazole,Z-heptadecyl imidazole, 4,5-diphenyl imidazole, 2,4,5-triphenylimidazole, 4,5-dicyclohexyl-l-cyclohexylmethyl imidazole, Z-cyclohexylimidazole, l-benzyl-2,4,5- triphenyl imidazole, 2-bromo-4(5)-methylimidazole, 4,5- dibromo imidazole, l-butyl-5-chloro--2-propyl imidazole,lallyl-4-(3,4 -dichloro-phenyl) imidazole, -benzyl-2- chloromethylimidazole, 2,4,5-triiodo imidazole, l-(B-oxyethyl) imidazole,4(5)-oxymethyl-5(4)-methyl imidazole,

5(4 )-(Boxyethyl) imidazole, 2-methyl-4( 5 )-nitro )-itro imidazole,4(5)-acetamide imidazole, 5(4)-amino-4(5)- methyl imidazole,l-(B-aminoethyl) imidazole, Z-(B- aminoethyl) imidazole, 4(5)-aminoethylimidazole, 4(5)- imidazole aldehyde, l-methyl imidazole-S-aldehyde, 2-imidazole phenylketone, 5(4)-acetyl-4(5)-methyl imidazole,4-methyl-l-imidazole carboxylic acid ethyl ester, 2-imidazole carboxylicacid, sodium 4,5-imidazole dicarboxylate, zinc 2- ethyl-4,5 -imidazoledicarboxylate, manganese 4(5)-methyl-5 (4)-imidazole carboxylate,l-methyl-4l-nitro-5-imidazole carboxylic acid,S-amino-lmethyl4-imidazole carboxylic acid ethyl ester, magnesium2-acetamide-4,5-imidazole dicarboxylate, Z-mercapto imidazole,l-(B-oxyethyl)-2-mercapto imidazole, 2-mercapto-4(5)imidazole carboxylicacid, 4(5)- phenyl-l-imidazole sulfonic acid, Z-imidazole sulfonic acid,4(5)-imidazole sulfonic acid, 4(5 )-methyl-5(4)-imidazole sulfonic acid,etc.

The polyamides to be applied to the method of the present inventioninclude homopolyamides and copolyamides obtained by polycondensation ofat least one polyamide-forming compound selected from the groupconsisting of lactams, waminocarboxylic acids and salts of diamines anddicarboxylic acids, for example, the polyamide-forming materials, suchas, y-butyrolactam, 6-valerolactam, e-caprolactam, heptolactam,

6amino caproic acid, 7-aminoheptanoic acid, 9- aminononanoic acid,-aminoudecanoic acid or salts of diamines, such as,tetramethylenediamine, pentamethylenediamine, hexamethylenediamine,heptamethylenediamine, octamethylene diamine, nonamethylenediamine,decamethylenediamine, un-

decamethylenediamine, dodecamethylenediamine, metaxylylene-diamine,paraxylylenediamine, bis('yaminopropyl)ether, N,N'-bis(w-aminopropyl)piperazine and l,l1-diaminoundecanone-6with dicarboxylic acids, such as,terephthalic acid, isophthalic acid, glutaric acid, adipic acid, pimelicacid, suberic acid, azelaic acid, sebacic acid, dodecandicarboxylicacid, hexahydroterephthalic acid, diphenylene- 4,4'-dicarboxylic acid,diphenylmethane-4,4' -dicarboxylic acid, diphenylether-4,4'-dicarboxylicacid and diphenylpropane-4,4'-dicarboxylic acid or salts of diamines anddicarboxylic acid derivatives or salts of diamine derivatives anddicarboxylic acids.

Furthermore, these polyamides may be added with inorganic or organicsubstances of delustrants, pigments, dyestuffs, light stabilizers, heatresistrants and plasticizers.

The polyolefins applicable to the present invention includepolyethylene, polypropylene, poly(butene-l poly 3-methylbutene-l etc.

An amount of imidazole or its derivatives added to the synthetic highpolymer is 0.005 to percent by weight, preferably 0.05-5.0 percent byweight.

When said amount is less than 0.005 percent by weight, the antistaticeffect is insufficient, while when said amount is more than 20 percentby weight, impact strength, breaking strength and the like of the shapedarticles are decreased, so that such amounts are not preferable. It isdesirable to select said amount properly within the above-describedrange depending upon the kind of the synthetic high polymers, theimidazole derivatives and the conditions in molding.

When the amount of imidazole or its derivatives added is within theabove-described range, the strength and elongation, dye receptivity,light stability and the like of the shaped articles are not varied.

Furthermore, the difference of substituent is said imidazole derivativesdoes not adversely affect on the antistatic effect.

A method for incorporating imidazole or its derivatives in the shapedarticles may be effected either by applying imidazole or its derivativesto fine particulates or fine powders of the synthetic high polymersuniformly and then directly melt molding the resulting fine particulatesor fine powders, or by melting the mixture of imidazole or itsderivative with the synthetic high polymer, molding once the melt intofine particulates or fine powders and then melt molding said fineparticulates or fine powders by a conventional process.

When the imidazole or its derivative is added to the polyamides, theaddition may be effected either into the starting materials of thepolyamide, during the polycondensation reaction, prior to completion ofthe reaction or into melted polyamide after completion of thepolycondensation reaction and in any process, said imidazole or itsderivatives can be dispersed lustrant is to be produced, imidazole orits derivative may be solely mixed with the high polymer according tothe abovementioned means, or a mixture of imidazole or its derivativewith additives, such as, pigment, dyestuff and delustrant may be addedto the polymer or starting materials thereof and dispersed homogeneouslytherein.

Any of the above-mentioned means for adding imidazole or its derivativeto the high polymer does not substantially influence on the remarkableantistatic effect.

lmidazole or its derivatives contained in the synthetic high polymerhave an excellent compatibility and retain a uniformly dispersed stateand the dispersibility is not decreased under normal molding conditions,such as, melt spinning extrusion molding, injection molding, andcompression molding. Furthermore, even if the polymer or the shapedarticles containing the imidazole derivative are washed with hot water,the imidazole derivative is not dissolved off.

Thus, the shaped articles of the synthetic high polymer treated with themethod of the present invention, show an excellent permanent antistaticeffect and do not cause stains due to dust absorbing property ordeposition of the antistatic agent and various conventional drawbacksdue to the electrification can be avoided in the production of the fiberor other shaped articles, the after-treatment and the practical use.

Accordingly, the synthetic high polymer according to the presentinvention is preferable for starting materials of production of variousclothings, interior ornaments and industrial goods as fiber or othermoldings.

The invention will be further explained in detail by the followingExamples: The part" means by weight.

EXAMPLE 1 Into an autoclave 100 parts of e-caprolactam, 3 parts ofwater, 0.3 part of titanium oxide, 0.18 part of acetic acid and apredetermined amount of imidazole derivatives were charged and mixed andthe atmosphere in the autoclave was substituted for gaseous nitrogen.Then the mixture was heated at 260 C. under a pressure of 1.5 kg./cm.(gauge pressure) for 3 hours and succeedingly, at 260 C. underatmospheric pressure for 2 hours to obtain primary polycondensate.Further, the polycondensation reaction was effected at 260 C. under areduced pressure of 300 mm. Hg for 5 hours and then the resultingpolycondensate was extruded in a string form from the bottom of theautoclave under a pressure of 3 kg./cm. (gauge pressure) of gaseousnitrogen atmosphere, passed through water bath and quenched andsolidified and then the resulting string was cut'into fine chips of 3mmflb X 3 mm.

On the other hand, as a control sample fine chips were made under thesame condition and in the same process as described above, except thatthe imidazole derivative was not contained.

The resulting chips were washed with hot water at 80 C. for 20 hours toremove water soluble components and then dried at 80 C. under a reducedpressure of 0.1 mm. Hg to obtain the chips having a water contentof0.067 percent by weight.

The thus-obtained dried fine chips were melt extruded through a nozzleby means of a heat-grid type melt-spinning apparatus after 40 minutesstay in molten state and the resulting undrawn filaments of 25ld/l8fwere wound on a bobbin without applying a spinning oil agent and thenthe resulting undrawn filaments were left to stand at 20 C. underpercent R.H. for 24 hours and cold drawn 3.59 times their originallength to obtain the drawn filaments of d/l 8f.

The strength and elongation and voltage of electrification andincorporated in the polyamide uniformly. 65 formed due to friction weremeasured with respect to each When a high polymer added with a pigment,dyestuff or dedrawn filament and the result is shown in the followingtable 1.

TABLE 1 Voltage of electrification (v.)

Addition Elon- Alter amount Strength gation Before 10 times Additivespercent (g./d.) percent cleaning cleaning Non addition 5. 34. 3 2, 2002, 200

l-benzyl imidazole b. 05 512 3113 58 60 l. 0 5. 3 30. 0 17 17 c. 32 5. Z1, 97 1, 2-1 td 11 id 1 0. 5.2 12

mp my m we 0. 5.2 32.8 43 65 1.0 5.0 31.3 12 3' 3? 3 33' 3 $33 $28 4, 11 1 0 5.3 .1

5 dlp icnyl midnzo e 0 05 5' 4 34. 3 75 80 1.0 5.2 36.4 18 0. 003 3 3g.3 2, egg 2, h 1 00.05 .1 3. c

bromo-4 met yl 1n1 dazole 0.05 5.2 31.2 70 75 1.0 5.2 33.5 15 2s 0. 005. 4 go. 7 1, 1, 1 0.00 5.3 2.4 4 mm) dazole 0. 05 5.1 35.1 83 so 1.05.3 34.7 20

As seen from table 1, when the amount of the imidazole derivative addedis less than 0.005 percent by weight, the antistatic effect is veryinsufficient, but if said amount is more than 0.005 percent by weight,the favorable antistatic effect can be obtained and particularly, ifsaid amount is more than 0.05,

percent by weight, the effect is remarkable and further is not decreasedeven by cleaning. Furthermore, the content of the additives does notafiect the strength and elongation adversely.

20 electrification was determined by means of a rotary static tester(made by Kowa Shokai).

The result is shown in table 2.

TABLE 2 Yarn property Addi- Spinning property Voltage of tionElongaelectriamount trength tion fication Additives (percent)Splunebihty Drawebillty (g. d.) (percent) (v.) Non addition Good Good5.0 32.5 1,800 Gong 00g... 5. 1 31.3 46 v -v imidazole '10313381333111::::;::d3:: 2:3 32:? i3 25 Yarn breakage Yarn breakage 4. 233. 1 10 occurred. occurred. 0.5 Good Good-.. 5.2 31.1 55 ZincQ-ethvHMmidmle dicarboxylm- 13 :11:38;:33:13:11381113332: 21% 3235 i3 25Yarn breakage Yarn breakage 4. 0 30. 6 15 occurred. occurred. 0. 5 6003Good 15.1 34. l 65 1-c-hvdwxyethynemmapwimidmle 18 1133113131:.::::S8:::::::::: E33 3832 i? 25 Yarn breakage Yarn breakage 4. 3 37. 115 occurred. occurred. 0.6 Goci G005! 5.0 30.5 5-phenyl'l'imidaloleSomme acid 13 :::::.18;:::::::::;::33.18:: 21% 33:3 i3 25 Yarn breakageYarn breakage 4.1 35.5 10

occurred. occurred.

EXAMPLEZ As seen from table 2, the imidazole derivatives have re- Into amixture of 90 p of capmlactam 10 parts of the markable antistaticeffect, but when the amount of the I I I 1 nt salt ofhexamethylenediamine with terephthalic acid, 0.18 lmidazole denvanvesadded ls more *3 25 R by weight, yarn breakage occurs frequently in thespinning and part of acetic acid and 0.4 part of titanium oxide wasadded a 50 drawing, and unevenness of draft is considerable in thecoldpredetermined amount of different imidazole derivatives as shown inthe following table 2 and after stirring and mixing drawing there areSerious dlmcu'mes m spmnab'my the resulting mixture was fed into areaction vessel and heated and drawabmty at 250 C. for 8 hours underatmospheric pressure under gase- EXAMPLE 3 ous nitrogen atmosphere toeffect polycondensation reaction.

The resulting polycondensate was extruded in a string form ch'ps ofPolyriexamethyleneadlpantlde were added from the bottom of the reactionvessel and passed through a Y Parent by weght of 'mlfiazofle derwauvesas w" water bath and quenched and solidified and then the solidified mthe table a Cubc'tYPe mlxer was fined String was cut into fi chips f 3q; x 3 mm the resulting mixture and tightly closed and then revolved ata AS a comm] sample fi chips f copolyamide containing rate of 5 r.p.m.for 2 hours, whereby the imidazole derivatives no imidazole derivativewere manufactured in the same were PP urrlformly the r:hrpsh chrps werefed manner and under the same condition as described above. intoextruder and p and the resuming filaments were P The resulting two kindsof fine chips were washed with hot plied with a Spinning agent theresulting undrawfl water and dried under a reduced pressure in the samemanner filaments d/1 gfwere lbctbbm I as described in example I to makethe water content 0.070 r r Sample; r ch1PS of.polyhexamethylerrefidrpa'percent by weight, and then the dried fine chips were melt-exmldecomammg rmldalole derrvallve were p "uded through a nozzle b means f a hapgrid type l same manner and under the same condition as describedspinning apparatus after 40 minutes stay in molten state and abovewereapplied with a spinning oil agent by revolving rollers, and Theresulrlrlg ur'drawrl were cold'drawn 356 [he resulting und awn filamentsof were wound on times their original length t0 Obtalfl drawn filamentsOf 8 bobbins respectively.

The resulting undrawn filaments were cold-drawn 3.69 times theiroriginal length to obtain drawn filaments of l00d/32f. which were woveninto taffetas respectively. The taffetas were scoured and dried, andafter left to stand for 24 hours at 20 C. under 65 percent R.H., thevoltage of electrifif. The drawn filaments were woven into taffeta,which was then scoured and determined with respect to the voltage ofelectrification in the same manner as described in the example 2.Further, the taffeta after scouring was washed 10 times repeatedly andthen the voltage of electrification was determined in the same manner asdescribed above.

The obtained result is shown in Table 3.

TABLE 3 Voltage of Yarn property electrification (v.)

Addition After 10 amount Strength Elongation Before times Additives(percent) (gn/d.) (percent) cleaning cleaning Non addition 5. 8 30. 5 2,300 2, 300 l-(B-aminoethyl) imidazole..- 0. 1 6. 6 35. 7 65 665-acety1-4-methyl imidazole 0. 1 5.8 31. 2 65 60 2cyclohexyl imidazole0.1 6.7 31.0 45 46 2-me th yl i-imidazole carboxylic acid 0.1 5.8 60 80As seen from table 3, the imidazole derivatives showed an excellentantistatic effect and the effect was not decreased even after thetafieta was washed l times. Furthermore, the decrease of the strengthand elongation of the drawn filament caused by incorporating imidazolederivatives did not substantially occur.

EXAMPLE 4 To 100 parts of polyethylene resin (Hi-zex 5,000 H, made byMitsui Sekiyu Kagaku Co.) was added a predetermined amount of imidazolederivatives as shown in the following table 4, stirred and mixed toobtain a homogeneous dispersion, which was extruded from an extruder toobtain a sheet TABLE 4 Surface Voltage of Added leakage electrificationamount resistance formed due to Additive (percent) (a) friction (v.)

None 8. 6X 10 6, 600 0. 003 2. lxigl z g, x

7. 1 l-octynmjdaz 016 982 1010 570 1. 0 3. x10 180 0. 003 3. 3X 5,2-heptadecyllmidazole 69g? 38 630 1. 0 3. 1X10 130 0. 003 a. oxrg z x 12,4,5-triphenylimldazoie 82 10m 780 1. 0 2. 8X10 200 0.003 2. 8X10:5-amino-4-methylimidazole- 9 982 2: 8 650 1. 0 3. 0X 10: 2302-mercapto-4-imidazole ear- 8 Eggs 2' boxylic acid As seen from table 4,when the amount of imidazole derivative added is less than 0.005 percentby weight, the effect for preventing electrification is extremely poor,but when the amount is more than 0.005 percent by weight, the effect isgood, and particularly when the amount is more than 0.05 percent byweight, the effect is remarkable.

EXAMPLE 5 To I00 parts of polypropylene resin (Noblen-8040, made byMitsubishi Yuka Co.) was added a predetermined amount of imidazolederivative as shown in the following table 5, stirred and mixed toobtain a homogeneous dispersion, which was then extruded from anextruder to obtain a sheet having a thickness of 1 mm. The extrusiontemperature was 240 C. (die).

As a control sample, a sheet containing no imidazole derivative wasmanufactured under the same condition as described above.

Each of the above-described sheets was determined with respect to thesurface leakage resistance and the voltage of As seen from table 5,imidazole derivatives have an excellent effect for preventingelectrification.

EXAMPLE 6 To parts of polystyrene resin (Styrol-HI-E, made by DenkiKagaku Kogyo Co.) was added and mixed a predetermined amount ofimidazole derivatives as shown in the following table 6 to obtain ahomogeneous dispersion, which was extruded from an extruder at atemperature of 240 C. to obtain a sheet having a thickness of 1 mm.

As a control sample, a polystyrene sheet containing no imidazolederivatives was manufactured under the same condition as describedabove.

Each of the above-mentioned sheets was determined with respect to thesurface leakage resistance and the voltage of electrification formed dueto friction to obtain a result as shown in table 6.

larly, have an excellent effect in more than 0.05 percent.

EXAMPLE 7 To 100 parts of powdery isotactic polypropylene (numberaverage molecular weight: 52,000) was added a predetermined amount ofimidazole derivatives as shown in the follow- Shown in table 8. ingtable 7 and fed into a melting apparatus, wherein the imidazolederivative was mixed with and dispersed in the polypropylenehomogeneously. Then the dispersion was TABLE 8 melted at 270 C. andextruded from nozzle in a string state, 5 Surface Voltage of Addedleakage electrificat on quenched and solidified. The solidified stringwas cut into amount resistance formed due to chips of 3 mmflb X 3 mm.Additive (percent) (9) friction (v.) i s a control sample, fine chipscontaining no imidazole None 43x10 3,400 derivative were manufactured inthe same manner as 0. 005 2. 8x10 2,200 l-phenylimidazole 0. 05 8. 5X 10800 q' 10 1. 2. 4x10 130 Fine chips of each sample were melt spun bymeans of an 0. 005 2. 6x10 2, 500 extruder to obtain a filament. Theresulting filament was z'undecynmidazole g 3-338: {23 determined withrespect to the surface leakage resistance and 2-methyl-4-lmldazole 0.005 3. 0 10 2, 700 the voltage of electrification formed due to frictionto obtain a cmblxync acid g 3' $13: 28 result as shown in table 7. l 5

TABLE 7 Yarn property Surface leaka 5 Voltage of electrificationresistance (9 formed due to friction (v). Added Spin- Elongaamountriabillty Stren th tion Before After Before After Additive (percent) (g.d.) (percent) washing washing washing washing None Good 6.0 20.5 76BX10765x" 2,900 2.350 0.5 Good.. 6.1 19.0 4.7 10 4.5X10 55 552-heptndecylimidazole 5.0 do 6.1 19.5 1.7 10 1.6X10 20 20 10 do 5.8 18.01.5)(10 1.5x10 15 25 Poor.-. 4.3 12.5 1.2X10 1.2X10 10 10 0 5 Good 5.917.5 5. 5X10 6.0X10 70 65 2-methyl-4-1midazole cerboxylic acid 5.0 ..-do6.1 16. 8 1. 8X10 1. 8X10 35 35 10 d0 6.7 17.5 1.3X109 1.3X10 15 15 25P00! 4.8 13.0 l.1X10 1.0X10 10 10 0.5 Good. 6.3 18.5 5. 9x10 c.0x1m 4550 5-phenyl-1-imidazole suli'onic acid 5. 0 do 6. 1 20. 3 2. 0X10 3X1 2010 ...d0 5.7 19.8 1.5)(10 1. 5x10 10 15 P001 4.3 14.1 1.0X10 1.2)(10 1010 As seen from table 7, the imidazole derivatives have a remarkableeffect for preventing electrification, but when the added amount is morethan 25 percent by weight, there is a serious difficulty inspinnability.

Furthen'nore, the effect for preventing electrification, the strengthand the elongation of the filament obtained by the above-mentionedtreatment are not decreased by washing.

EXAMPLE 8 To 100 parts of polyvinyl chloride resin (SS-100, made byDenki Kagaku Kogyo Co.) were added 50 parts of D.O.P., 1.5 parts ofcadmium stearate and 0.5 part of barium stearate as plasticizers, andfurther added a predetermined amount of imidazole derivatives as shownin the following table 8. The resulting mixture was stirred, mixed,further kneaded at 160 C. and then shaped into a sheet having athickness of 1 mm. by a press at 130 C. under kg./cm.

As a control sample, a sheet containing no imidazole derivative wasmanufactured under the same condition as described above.

Each of the above-described sheets was determined with respect to thesurface leakage resistance and the voltage of electrification formed dueto friction to obtain a result as formula N l R3 L wherein R ishydrogen, alkyl, aryl, aralkyl, cycloalkyl, carboxyl or metal saltthereof, alkylcarbonyl, oxyalkyl, aminoalkyl Ol' sulfo;

R is mercapto, halogen or a group as defined for R,;

and R and R are independently nitro or a group as defined for R 2. Thecomposition of claim 1, wherein said imidazole constitutes 0.05 to 5.0percent by weight based upon said homopolyamide or copolyamide.

2. The composition of claim 1, wherein said imidazole constitutes 0.05to 5.0 percent by weight based upon said homopolyamide or copolyamide.